I grew up on the North Side of Chicago during the seventies and eighties and was raised to love the woeful Cubs. Spare me your pity. Sure, my team never came close to a pennant. (They still haven't.) But we adapted. My grandmother, for instance, had cheered the team for 60 years and never celebrated a World Series title. Finally, she discovered it was better to read the standings upside down.

There were benefits to being a Cubs fan. I got to spend my summer days at Wrigley Field, where $2.00 bought a children's general-admission ticket and a seat just off the first-base line. In those days, the ballpark was usually deserted. My friends and I would show up for batting practice to chase autographs and foul balls. We joined the official fan clubs, and I got to meet my heroes: Bobby Murcer, Bill Buckner, Bruce Sutter, and Dave Kingman. Their flaws never bothered me. Sure, every year I dreamed of a championship, and every year these dreams were dashed. But my team had perfected the art of failure, and I never expected anything more.

Now I live in New York City, and I have a 3-year-old son. Of course, I wanted him to fall for Chicago's lovable losers. A hometown team would be better, I knew. But I grew up in the shadow of the Miracle Mets of 1969, and I still resent them. The Yankees? God forbid. With 26 titles and the culture of entitlement that comes with them, the franchise offends those of us raised in Wrigleyville. So really, what choice did I have?

Also, I admit, I believed that my son might be the one we'd been waiting for, the guy who would turn the Cubs' luck around. And then something incredible happened. In 2007, his first full season, the Cubs made the playoffs. My grandmother bought him a cap and T-shirt. I persuaded my wife to let him stay up late to watch the games on TV. I'll confess that it hurt when the Diamondbacks swept us 3–0 in the first round. But we were off to a promising start.

The next year was better. The Cubs were sensational all season. They cruised into the playoffs with the best record in the National League and had home-field advantage against the Dodgers. Once again, I outfitted my boy in Cubs regalia and got him permission to stay up late to watch the games. I taught him to say Soriano, Lee, and, yes, Fukudome, to sing "root, root, root for the Cubbies" during the seventh-inning stretch.

But it didn't matter. The Cubs lost the first game of the NLDS badly, the second game worse. Then they went to Los Angeles and were swept again. I couldn't help asking: What was I doing to my child?

This year I vowed to do things differently. No, I didn't renounce the Cubs. But I didn't replace his Cubs cap when he lost it, either. In June I did the unthinkable: I bought him a Yankees hat, classic black, then another, in red. I got us tickets to see the Red Sox at the new ballpark. Gave him a baseball signed by all the Yankees and a plastic batting helmet filled with ice cream. We started reading the sports page together, cheering each time the Yankees triumphed. "I love the Yankees because they're the winners," he announced one day. And though I smiled, I also felt my heart sink.

Last week, the Yankees won their 27th World Series. Yes, those of us from Chicago are counting, too. My son was jubilant. He learned to say Matsui, made the Yankees symbol with Play-Doh, and asked if we could go to the parade.

Part of me wonders if I did the right thing. My son is now a Yankees fan, as is his birthright, and so he carries a burden. He may never be content in a second city. He may expect, even demand, a championship each year. He may not develop the character that comes from enduring disappointment, nor have faith that fidelity and suffering will be rewarded someday.

Then again, he has already experienced a World Series title, something neither my grandmother (now 91) nor I have done. I suppose I'm a bit envious, but mostly I'm enjoying his — okay, our, November happiness.

Maybe next year I'll get my own Yankees cap. Then again, next year may belong to the Cubs.